Pet-friendly holiday rentals in Pittsfield
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Top-rated pet-friendly home rentals in Pittsfield
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Pittsfield pet-friendly home rentals
Pet-friendly house rentals
Home in Pittsfield
4.83 out of 5 average rating, 221 reviewsKillington area home - 4-seasons & hot tub
31 Oct – 7 Nov
Home in Rochester
4.93 out of 5 average rating, 202 reviewsPorch House
11–18 Jun
Home in Mendon
4.88 out of 5 average rating, 210 reviewsRanch at Mendon Mt Orchards
9–16 Jun
Home in Rochester
4.94 out of 5 average rating, 181 reviewsThe McKinley House
3–10 Feb
Home in Roxbury
4.9 out of 5 average rating, 157 reviewsCaptain Tom's Cabin - Secluded Vermont Getaway
29 Sep – 6 Oct
Home in Granville
4.95 out of 5 average rating, 107 reviewsEpic Views of the Green Mountains
Home in Woodstock
5.0 out of 5 average rating, 110 reviewsBeautiful Woodstock Home-Perfect for entertaining
17–24 Sep
Home in Newbury
4.97 out of 5 average rating, 114 reviewsWright’s Mountain Retreat with Sauna
31 Mar – 7 Apr
Pet-friendly home rentals with a pool
Townhouse in Killington
4.93 out of 5 average rating, 199 reviewsSpacious 2 Bed/2 Bath Dogs Allowed, Spa Onsite
20–27 Jun
Guest house in Granville
4.9 out of 5 average rating, 786 reviewsMoon Valley Country Retreat no clean fee pets yes
9–16 Mar
Flat in Clarendon
4.92 out of 5 average rating, 133 reviewsVermont Horse Farm
25 Jul – 1 Aug
Apartment in Killington
4.96 out of 5 average rating, 103 reviewsCozyCub Pets, AC, Bike to Mtn, Fireplace, Walk out
30 Nov – 7 Dec
Townhouse in Killington
4.88 out of 5 average rating, 220 reviewsRenovated 2bd/2.5bath/Den + Pool Access (pets ok)
2–9 Aug
Cabin in Bridport
4.92 out of 5 average rating, 133 reviewsChamplain Valley Alpacas
12–19 Oct
Cabin in Warren
4.83 out of 5 average rating, 220 reviewsBunny Hill Cabin -Pets, Shared Hot Tub & Lap Pool
29 Jul – 5 Aug
Flat in Barre
4.94 out of 5 average rating, 156 reviewsRelax in Recreation Paradise!
10–17 Sep
Private, pet-friendly home rentals
Cabin in Fair Haven
4.97 out of 5 average rating, 152 reviewsPrivate and cozy cabin with Lake Bomoseen views!
14–21 Nov
Flat in Stockbridge
4.88 out of 5 average rating, 160 reviewsRustic 64 Acre Woodland Haven on a Beautiful River
30 Sep – 7 Oct
Cabin in Wells
4.95 out of 5 average rating, 151 reviewsGatsby's Getaway
29 May – 5 Jun
Treehouse in Hancock
4.94 out of 5 average rating, 641 reviewsThe Beaver Pond Treehouse @ Vermont ReTREEt
11–18 Sep
Cabin in Granville
4.99 out of 5 average rating, 134 reviewsQuaint log cabin nestled in the woods
25 Jan – 1 Feb
Cottage in Lincoln
4.87 out of 5 average rating, 857 reviewsThe Barn at North Orchard, Near Middlebury
9–16 Dec
Tiny home in Clarendon
4.88 out of 5 average rating, 173 reviewsSecluded tiny house resort - DOG FRIENDLY
31 Aug – 7 Sep
Guest house in Hartland
4.95 out of 5 average rating, 913 reviewsYurt In The Woods - Private Refuge
26 Mar – 2 Apr
Quick stats about holiday rentals that are pet-friendly in Pittsfield
Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
870 reviews
Nightly prices starting at
€ 112 before taxes and fees
Destinations to explore
- Burlington Holiday rentals
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- Pet-friendly rentals Vermont
- Pet-friendly rentals Vermont
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- Rentals with a fireplace Pittsfield
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- Monthly Rentals Pittsfield
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